The insanity of dating

Being almost 40 and single, I’ve discovered lots of advice on dating; much of it not paradoxical but a merely a minefield. Relationships are chemical not mechanical, and there’s no single or simple solution.

How do we go about remedying the situation? (I use the phrase deliberately.) The following is a gallimaufry of what I’ve heard/read/thought. And my apologies, ladies, this is from a guy’s perspective, but all contributions gratefully accepted.

The chief piece of advice I’ve heard is: pursue her. This is difficult because we fear rejection. Sure you might be but what if you aren’t? But if she does say no, take it as no. This is difficult, especially if you get on well in every way except, for some reason, she isn’t romantically interested in you. But on the other hand, I know guys who have continued the pursuit even though she’s said no. (Although, knowing their character, they weren’t obnoxious about it.) One guy I know asked a girl out thirteen times, over two years, before she agreed to go out with him. They did get married. Again, there’s no rule: it depends upon each person.

If she does say no but you believe she’s worth pursuing, what then? Pursue her slowly and courteously and hope her feelings will change? If they do, you’ll be another statistic encouraging perseverance. What if her feelings don’t change? Do you stop pursuing her and focus on being her friend, and hope her feelings will change? Or ignore your feelings and move on? If you do call off the pursuit, when? Months? Years? Waiting for something that may or may not happen? Or on the other hand, what if you give up after she’s said no, when a little pursuit would have won her? If the guy I just mentioned did that, he might still be single.

Face it, there’s no easy solution. Pursue her. Don’t pursue her. Persevere: maybe her feelings will change. Don’t persevere: wait for your feelings for her to go away. Date other women, and show her you’re mature enough to let go. Or don’t date other women, and show her how serious you are about her.

Some people would say this is the marvellous mystery of romance. Such people are all happily involved in relationships. Being single, my opinion is that it’s a pain and the emotional rollercoaster isn’t worth the uncertainty of “what do I do? Pursue her or let it go? Keep hoping or try to kill that hope?” Whatever you do, whether you remain single or get married, you’re going to suffer. There’ll be uncertainly, hope and despair, joy and misery. Maybe it will all work out; maybe it won’t. But hope is difficult to kill. Anyone had any joy in such homicide?

My only cold comfort is I’d rather be single and wish I were married than the other way around.